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A lot of great responses to this from great contributors. Here is another point of view. (Full disclosure: We have sites each way).

If you consider a title a title and a heading a heading, the H1 would be different, but still on subject. I know of no empirical data that states a slightly differing H1 is a negative from an SEO perspective but keyword usage in H1 may provide some benefit. If the title is Used Cars Denver, to me, it makes no sense from a writing perspective to make the H1 Used Cars Denver. I think a reader gets that the title brought her here, so you use a variant in the first part (H1) of the content: Used Cars Denver - Under 10,000 miles. You still have your keyword, but you are giving the reader (searcher) more depth in the next paragraph.

Obviously, the H2 could be Used Cars Denver - 10001 to 25,000, etc.

Even though we do it, I think part of it is driven by tools we use for keyword optimization on page (think SEOmoz Pro Onpage Optimization Grader) as opposed to what might be more readable or potentially more SEO friendly. Yes, I know about keywords in the H1, etc. but I do not think you have to match the title tag. I think it has to make sense from a reading perspective or you are just being redundant. Again, we do both... But, maybe I will revisit this ;)

I think they should be slightly different. Obviously on a case by case basis, but I tend to have more content in my page title then in the H1. I do start my page titles with the H1 but I may include a strong brand name or even a call to action in an effort to increase CTR. It's also good practice to match H1 with page name / URL.

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